Pyrazole derivatives for controlling arthropods

Abstract

The present invention relates to novel halogen-substituted compounds, to processes for their preparation and to their use for controlling animal pests, in particular arthropods and especially insects and arachnids.

1 . A compound of formula (I) 
       
         
           
           
               
               
           
         
       
       wherein
 L is linear C 1 -C 4  alkanediyl, C 2 -C 4  alkenediyl or C 2 -C 4  alkynediyl, each of which may be substituted with one or more groups independently selected from halogen, C 1 -C 4  alkyl and C 3 -C 6 -cycloalkyl, wherein two C 1 -C 4 -alkyl substituents may form a ring together with the carbon atom to which they are bonded; or 
 a moiety (CH 2 ) n —X—(CH 2 ) m  wherein 
 n and m are independently 0, 1 or 2 and 
 X is selected from a group X 1 , X 2 , X 3  or X 4 , wherein 
 X 1  is C 3 -C 7 -cycloalkanediyl, which is optionally substituted with 1 to 3 substituents selected from halogen, cyano, and C 1 -C 4  alkyl, wherein (CH 2 ) n — and (CH 2 ) m — may be attached either to the same or to different carbon atoms of X 1 ; or 
 X 2  is phenylene, which is optionally substituted with 1 to 4 substituents selected from halogen, cyano, and C 1 -C 4  alkyl; or 
 X 3  is C 5 -C 6 -heteroarenediyl, which is optionally substituted with 1, 2 or 3 substituents selected from halogen, cyano, and C 1 -C 4  alkyl; or 
 X 4  is C 5 -C 8  bicycloalkanediyl, which is optionally substituted with 1 to 4 substituents selected from halogen, cyano, and C 1 -C 4  alkyl wherein (CH 2 ) n — and (CH 2 ) m — may be attached either to the same or to different carbon atoms of X 4 ; and 
 Y is selected from a group (T 1 ) 
 
       
         
           
           
               
               
           
         
       
       wherein
 R 1 , R 2  and R 3  are each independently selected from hydrogen, halogen, cyano, nitro, linear or branched C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, halogen-substituted linear or branched C 1 -C 6 -alkyl, halogen-substituted C 1 -C 6 -alkoxy, halogen substituted C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, N,N-di-C 1 -C 6 -alkylamino, N—C 1 -C 3 -alkoxy-C 1 -C 4 -alkylamino and 1-pyrrolidinyl
 or from a group (T 2 ) 
 
 
       
         
           
           
               
               
           
         
       
       wherein
 Z 1  and Z 2  are each independently selected from hydrogen, halogen, cyano, nitro, linear or branched C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halogen-substituted linear or branched C 1 -C 6 -alkyl, halogen-substituted C 1 -C 6 -alkoxy, halogen substituted C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, N,N-di-C 1 -C 6 -alkylamino, N—C 1 -C 3 -alkoxy-C 1 -C 4 -alkylamino and 1-pyrrolidinyl; and 
 Z 3  represents hydrogen, linear or branched C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl or hetaryl, each of which may be substituted with 1 to 5 substituents selected from hydroxy, halogen, cyano, nitro, amino, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl and phenyl; 
 And/or a salt thereof. 
 
     
     
         2 . The compound according to  claim 1 , wherein
 L is linear C 1 -C 4  alkanediyl or C 2 -C 4  alkenediyl, each of which may be substituted with one or more groups independently selected from halogen, C 1 -C 4  alkyl and C 3 -C 6  cycloalkyl, wherein two C 1 -C 4 -alkyl substituents may form a ring together with the carbon atom to which they are bonded; or   a moiety (CH 2 ) n —X—(CH 2 ) m  wherein   n and m are independently 0, 1 or 2 and   X is selected from a group X 1 , X 2 , X 3  or X4 as defined in  claim 1 ; and   Y is selected from a group (T 1 ) or (T 2 ) as defined in  claim 1 ;   And/or a salt thereof.   
     
     
         3 . The compound according to  claim 1 , wherein
 L is linear C 1 -C 4  alkanediyl or C 2 -C 4  alkenediyl, each of which may be substituted with one or more groups independently selected from halogen, C 1 -C 4  alkyl and C 3 -C 6  cycloalkyl, wherein two C 1 -C 4 -alkyl substituents may form a ring together with the carbon atom to which they are bonded; or   a moiety (CH 2 ) n —X—(CH 2 ) m  wherein   n and m are independently 0, 1 or 2 and   X is selected from a group X 1  or X 2  as defined in  claim 1 ; and   Y is selected from a group (T 1 ) or (T 2 ) as defined in  claim 1 ;   And/or a salt thereof.   
     
     
         4 . The compound according to  claim 1 , wherein
 Y is selected from a group (T 1 )   
       
         
           
           
               
               
           
         
         
           wherein 
         
         R 1 , R 2  and R 3  are each independently selected from hydrogen, halogen, linear or branched C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 3 -alkoxy, linear or branched halogen-substituted C 1 -C 3 -alkyl, halogen-substituted C 1 -C 3 -alkoxy, halogen substituted C 3 -C 6 -cycloalkyl, and 1-pyrrolidinyl, optionally R 1 , R 2  and R 3  are each independently selected from halogen, linear or branched halogen-substituted C 1 -C 3 -alkyl, and halogen-substituted C 1 -C 3 -alkoxy;
 or from a group (T 2 ) 
 
       
       
         
           
           
               
               
           
         
       
       wherein
 Z 1  represents linear or branched C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 3 -alkoxy, which may independently of one another be substituted with 1 to 5 substituents selected from hydroxy, halogen, cyano, nitro, C 1 -C 3 -alkyl, and C 1 -C 3 -alkoxy; 
 optionally Z 1  represents linear or branched C 1 -C 3 -alkyl or C 3 -C 6 -cycloalkyl, which may independently of one another be substituted with 1 to 5 halogen substituents; 
 Z 2  represents halogen, cyano, nitro, amino, or linear or branched C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, which may independently of one another be substituted with 1 to 5 substituents selected from hydroxy, halogen, cyano, nitro, C 1 -C 3 -alkyl, and C 1 -C 3 -alkoxy; 
 optionally Z 2  represents linear or branched C 1 -C 3 -alkyl, which may be substituted with 1 to 5 halogen substituents, optionally with 1 to 3 halogen substituents, optionally trifluoromethyl or Z 2  represents nitro, methylsulphanyl, methylsulphinyl, methylsulphonyl, fluorine, chlorine, bromine, iodine; and 
 Z 3  represents hydrogen or linear or branched C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl or hetaryl, which may independently of one another be substituted with 1 to 5 substituents selected from hydroxy, halogen, cyano, nitro, C 1 -C 3 -alkyl, and C 1 -C 3 -alkoxy; 
 optionally Z 3  represents hydrogen or linear or branched C 1 -C 6 -alkyl which may be substituted with 1 to 5 substituents selected from hydroxy, halogen, C 1 -C 3 -alkyl, and C 1 -C 3 -alkoxy; 
 And/or a salt thereof. 
 
     
     
         5 . The compound according to  claim 1 , wherein
 Y is selected from a group (T 1 )   
       
         
           
           
               
               
           
         
         
           wherein 
         
         R 1  is halogen, optionally fluorine, bromine or chlorine, optionally chlorine; 
         R 2  is linear or branched C 1 -C 3 -alkyl substituted with 1 to 7 halogen, optionally linear or branched C 1 -C 3 -alkyl substituted with 1 to 7 fluorine, optionally CF 3 , C 2 F 5  or C 3 F 7 ; and 
         R 3  is C 1 -C 3 -alkoxy substituted with 1 to 3 halogen, optionally C 1 -C 3 -alkoxy substituted with 1 to 3 fluorine, optionally OCF 3 , OC 2 F 5  or OC 3 F 7 ; 
         or from a group (T 2 ) 
       
       
         
           
           
               
               
           
         
       
       wherein
 Z 1  represents linear or branched C 1 -C 3 -alkyl or C 3 -C 6 -cycloalkyl, substituted with 1 to 5 halogen substituents, optionally trifluoromethyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl or pentafluoroethyl, optionally trifluoromethyl or pentafluoroethyl; 
 Z 2  represents linear or branched C 1 -C 3 -alkyl substituted with 1 to 3 halogen substituents, nitro, methylsulphanyl, methylsulphinyl, methylsulphonyl, fluorine, chlorine, bromine, or iodine; 
 optionally Z 2  represents linear or branched C 1 -C 3 -alkyl substituted with 1 to 3 fluorine, optionally trifluoromethyl; and 
 Z 3  represents hydrogen or linear or branched C 1 -C 6 -alkyl, optionally linear or branched C 1 -C 6 -alkyl, optionally hydrogen, methyl, ethyl, or n-propyl; 
 And/or a salt thereof. 
 
     
     
         6 . The compound according to  claim 1 , wherein the group (T 1 ) is represented by one of the following groups (T1-1), (T1-2) or (T2-1): 
       
         
           
           
               
               
           
         
         And/or a salt thereof. 
       
     
     
         7 . The compound according to  claim 1 , wherein
 L is linear C 2 -C 4  alkanediyl or C 2 -C 4  alkenediyl, each of which may be substituted with one or more groups independently selected from halogen and C 1 -C 4  alkyl;   And/or a salt thereof.   
     
     
         8 . The compound according to  claim 1 , wherein
 L is a moiety (CH 2 ) n —X 1 —(CH 2 ) m  wherein   n and m are independently 0, 1 or 2 and   X 1  is C 3 -C 6 -cycloalkanediyl, which is optionally substituted with 1 to 3 substituents selected from halogen, cyano, and C 1 -C 4  alkyl, wherein (CH 2 ) n — and (CH 2 ) m — may be attached either to the same or to different carbon atoms of X 1 ;   And/or a salt thereof.   
     
     
         9 . The compound according to  claim 1 , wherein
 L is a moiety (CH 2 ) n —X 2 —(CH 2 ) m  wherein   n and m are independently 0, 1 or 2 and   X 2  is phenylene, which is optionally substituted with 1 to 4 substituents selected from halogen, cyano, and C 1 -C 4  alkyl;   And/or a salt thereof.   
     
     
         10 . The compound and/or salt according to  claim 1  for use as a medicament. 
     
     
         11 . A pharmaceutical composition comprising at least one compound according to  claim 1 , which optionally comprises at least one further component selected from auxiliaries, excipients, solvents and/or at least one additional pharmaceutically active agent. 
     
     
         12 . The pharmaceutical composition according to  claim 11  for subcutaneous or oral application. 
     
     
         13 . A product comprising the compound or the pharmaceutical according to  claim 1  for controlling one or more parasites on animals, optionally for controlling insects optionally fleas, and arachnids, optionally selected from the group of Chelicerata, optionally ticks, acari and mites, optionally on companion animals optionally cats and dogs. 
     
     
         14 . A process for preparing the compound according to  claim 1 , comprising reacting a compound (A) 
       
         
           
           
               
               
           
         
       
       with a group (B) 
       
         
           
           
               
               
           
         
       
       wherein
 R x  represents hydrogen and R y  represents a —CH 2 —Cl group or 
 R x  represents a —CH 2 —OH group and R y  represents hydrogen; 
 
       wherein
 PG represents a protecting group or hydrogen to form the compound according to formula (I) and/or salt thereof, 
 and wherein in cases wherein PG is not hydrogen, deprotection is carried out to form the compound (I). 
 
     
     
         15 . A process according to  claim 14 , further comprising
 in the case that R x  represents hydrogen and R represents a —CH 2 —Cl group, preparing the group (B) with R y =—CH 2 —Cl (compound (B-2)) from a compound (B-1)   
       
         
           
           
               
               
           
         
       
       or
 in the case that R x  represents a —CH 2 —OH group and R y  represents hydrogen, 
 preparing the group (A) with R x =—CH 2 —OH (compound A-3)) from a compound (A-1) via an intermediate compound (A-2) 
 
       
         
           
           
               
               
           
         
       
     
     
         16 . An intermediate compound according to formula (C) 
       
         
           
           
               
               
           
         
       
       wherein
 L is linear C 1 -C 4  alkanediyl, C 2 -C 4  alkenediyl or C 2 -C 4  alkenediyl, each of which may be substituted with one or more groups independently selected from halogen, C 1 -C 4  alkyl and C 3 -C 6 -cycloalkyl, wherein two C 1 -C 4 -alkyl substituents may form a ring together with the carbon atom to which they are bonded; or 
 a moiety (CH 2 ) n —X—(CH 2 ) m  wherein 
 n and m are independently 0, 1 or 2 
 X is selected from a group X 1 , X 2 , X 3  or X 4 , wherein 
 X 1  is C 3 -C 7 -cycloalkanediyl, which is optionally substituted with 1 to 3 substituents selected from halogen, cyano, and C 1 -C 4  alkyl, wherein (CH 2 ) n — and (CH 2 ) m — may be attached either to the same or to different carbon atoms of X 1 ; or 
 X 2  is phenylene, which is optionally substituted with 1 to 4 substituents selected from halogen, cyano, and C 1 -C 4  alkyl; or 
 X 3  is C 5 -C 6 -heteroarenediyl, which is optionally substituted with 1, 2 or 3 substituents selected from halogen, cyano, and C 1 -C 4  alkyl; or 
 X 4  is C 5 -C 8  bicycloalkanediyl, which is optionally substituted with 1 to 4 substituents selected from halogen, cyano, and C 1 -C 4  alkyl wherein (CH 2 ) n — and (CH 2 ) m — may be attached either to the same or to different carbon atoms of X 4 ; and 
 Y is selected from a group (T 1 ) 
 
       
         
           
           
               
               
           
         
       
       wherein
 R 1 , R 2  and R 3  are each independently selected from hydrogen, halogen, cyano, nitro, linear or branched C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, halogen-substituted linear or branched C 1 -C 6 -alkyl, halogen-substituted C 1 -C 6 -alkoxy, halogen substituted C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, N,N-di-C 1 -C 6 -alkylamino, N—C 1 -C 3 -alkoxy-C 1 -C 4 -alkylamino and 1-pyrrolidinyl
 or from a group (T 2 ) 
 
 
       
         
           
           
               
               
           
         
       
       wherein
 Z 1  and Z 2  are each independently selected from hydrogen, halogen, cyano, nitro, linear or branched C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halogen-substituted linear or branched C 1 -C 6 -alkyl, halogen-substituted C 1 -C 6 -alkoxy, halogen substituted C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, N,N-di-C 1 -C 6 -alkylamino, N—C 1 -C 3 -alkoxy-C 1 -C 4 -alkylamino and 1-pyrrolidinyl; and 
 Z 3  represents hydrogen, linear or branched C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl or hetaryl, each of which may be substituted with 1 to 5 substituents selected from hydroxy, halogen, cyano, nitro, amino, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl and phenyl; 
 and wherein PG represents a tert-butyl group; 
 or according to formula (A-3)